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Acetone

Acetone
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Sample of acetone
Names
Preferred IUPAC name
Propan-2-one
Other names
  • Acetone
  • Dimethyl ketone
  • Dimethyl carbonyl
  • β-Ketopropane
  • Propanone
  • 2-Propanone
  • Dimethyl formaldehyde
  • Pyroacetic spirit (archaic)
  • Ketone propane
Identifiers
67-64-1 YesY
3D model (Jmol) Interactive image
3DMet B00058
Abbreviations DMK
635680
ChEBI CHEBI:15347 YesY
ChEMBL ChEMBL14253 YesY
ChemSpider 175 YesY
ECHA InfoCard 100.000.602
EC Number 200-662-2
1466
KEGG D02311 YesY
MeSH Acetone
PubChem 180
RTECS number AL3150000
UNII 1364PS73AF YesY
UN number 1090
Properties
C3H6O
Molar mass 58.08 g·mol−1
Appearance colorless liquid
Odor pungent, irritating, floral
Density 0.7845 g cm−3 (25 °C)
Melting point −94.7 °C (−138.5 °F; 178.5 K)
Boiling point 56.05 °C (132.89 °F; 329.20 K)
miscible
Solubility miscible in benzene, diethyl ether, methanol, chloroform, ethanol
log P −0.042
Vapor pressure 9.39 kPa (0 °C)
30.6 kPa (25 °C)
374 kPa (100 °C)
2.8 MPa (200 °C)
Acidity (pKa) 19.2
Basicity (pKb) −5.2 (for conjugate base)
-33.78·10−6 cm3/mol
1.3588 (VD=54.46)
Viscosity 0.295 mPa·s (25 °C)
Structure
Trigonal planar at C2
Dihedral at C2
2.91 D
Thermochemistry
125.45 J/mol·K
200.4 J/mol·K
−250.03-(−248.77) kJ/mol
−1.772 MJ/mol
Hazards
Safety data sheet See: data page
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H319, H336
P210, P261, P305+351+338
Highly Flammable F Irritant Xi
R-phrases R11, R36, R66, R67
S-phrases (S2), S9, S16, S26
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −20 °C (−4 °F; 253 K)
465 °C (869 °F; 738 K)
Explosive limits 2.6–12.8%
1185 mg/m3 (TWA), 2375 mg/m3 (STEL)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
5800 mg/kg (rat, oral)
3000 mg/kg (mouse, oral)
5340 mg/kg (rabbit, oral)
20,702 ppm (rat, 8 hr)
45,455 ppm (mouse, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
1000 ppm (2400 mg/m3)
REL (Recommended)
TWA 250 ppm (590 mg/m3)
IDLH (Immediate danger)
2500 ppm
Related compounds
Related compounds
Butanone
Isopropanol
Urea
Carbonic acid
Carbonyl fluoride
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Acetone (systematically named 2-propanone) is the organic compound with the formula (CH3)2CO. It is a colorless, volatile, flammable liquid, and is the simplest ketone.

Acetone is miscible with water and serves as an important solvent in its own right, typically for cleaning purposes in the laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate and bisphenol A. It is a common building block in organic chemistry. Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner.

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetes produce it in larger amounts. Reproductive toxicity tests show that it has low potential to cause reproductive problems. Pregnant women, nursing mothers and children have higher levels of acetone.Ketogenic diets that increase acetone in the body are used to counter epileptic attacks in infants and children who suffer from recalcitrant refractory epilepsy.

Acetone was first produced by alchemists during the late Middle Ages via the dry distillation of metal acetates (e.g., lead acetate, which produced "spirit of Saturn" (since the alchemical symbol for lead was also the astrological symbol for the planet Saturn)).

In 1832, French chemist Jean Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone. In 1833, the French chemist Antoine Bussy named acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid). By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl; the following year, the French chemist Charles Frédéric Gerhardt concurred. In 1865, the German chemist August Kekulé published the modern structural formula for acetone.


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Wikipedia

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